HCID 14171585, compound → Zaldaride

HRID 845379Notes

Reaction equation

HRID 845379 reaction equation
[CH3:1][C:2]1([C:16]([N:18]2[CH2:23][CH2:22][CH:21]([N:24]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[NH:26][C:25]3=[O:33])[CH2:20][CH2:19]2)=O)[O:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]2[CH:13]=[CH:14][CH:15]=[C:3]12.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.CCOCC>[CH3:1][C:2]1([CH2:16][N:18]2[CH2:19][CH2:20][CH:21]([N:24]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[NH:26][C:25]3=[O:33])[CH2:22][CH2:23]2)[O:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]2[CH:13]=[CH:14][CH:15]=[C:3]12

Participants

5

Reactant 2

HCID 14171585HCID 14171585, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 65909Zaldaride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3.0 g of 1,3-dihydro-1-{1-[(4-methyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)carbonyl]-4-piperidinyl}-2H-benzimidazol-2-one in 120 ml of tetrahydrofuran is added 700 mg of lithium aluminum hydride. The reaction mixture is then heated at reflux temperature for 6 hours followed by stirring at room temperature for 18 hours. The reaction mixture is diluted with 150 ml of ether and the excess lithium aluminum hydride destroyed in the usual manner described below. The resulting granular precipitate is removed by filtration. The organic phase is washed with 150 ml of dilute sodium hydroxide and then 150 ml of brine. The organic extracts are then dried over magnesium sulfate, filtered and solvent evaporated under reduced pressure to yield 1,3-dihydro-1-{1-[(4-methyl-4H,6H-pyrrolo[1,2-a][4,1]-benzoxazepin-4-yl)-methyl]-4-piperidinyl}-2H-benzimidazol-2-one, m.p. 199°-201°, the compound of formula II wherein R1 and R5 =H, and R2 =CH3 and n=1.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureat reflux temperature for 6 hours
  3. customthe excess lithium aluminum hydride destroyed in the usual manner
  4. customThe resulting granular precipitate is removed by filtration
  5. washThe organic phase is washed with 150 ml of dilute sodium hydroxide
  6. dry with materialThe organic extracts are then dried over magnesium sulfate
  7. filtrationfiltered
  8. customsolvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-ff370d29e23a478898590d2eed8928c0
Source dataset
uspto-grants-1988_07
Patent number
US04758559

Reaction notes

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